It’s the kind of sunny, Sunday drive you might dream about: Rambling along a quiet, two-lane road that leads up the fertile flanks of an ancient volcano, views of green valleys and wild Pacific waves revealing themselves at almost every turn. 

I’m on the island of Maui, steering my mid-size rental Chrysler toward the summit of Mount Haleakala on a quest to get to know the Aloha State by road. While Maui’s beaches have always tempted me to simply put up my feet and relax by the water, it remains true that this Hawaiian island is one of the best places in the United States to take a scenic drive—or a few.

Going Upcountry

Surfing Goat Dairy, photo by Alexandra Baackes

I start my road-tripping with a drive through Upcountry Maui. Sitting roughly halfway between Maui’s capital in Wailuku and the peak of Haleakala, this region is incredibly fertile, with a year-round growing season that benefits from a combination of rich, volcanic soil and plenty of precipitation.

As I drive along Baldwin Avenue, I spot a line of pickup trucks parked in front of a series of Wild West wooden storefronts. It’s a strange site—a scene from a Texas cowtown, seemingly transported to the heart of the Pacific.

I’ve arrived at Makawao, home to Maui’s cattle wranglers (known as paniolo) since the 19th century. Upcountry Maui beef is some of the best in the world (ranched nearby), and Makawao still hosts an annual rodeo every Fourth of July. I park next to a pickup and take a slow stroll through the town’s galleries and museums—there’s a prolific arts community here—before stopping in at the famous T. Komoda Store & Bakery. Established in 1916, this locally loved spot is best-known for its cream puffs, which often sell out to a hungry crowd that lines up out the door every morning.

Happy to have scored some baked goods, I’m off to sample more of Upcountry’s edible treasures. I navigate across Haleakala’s slopes on a stretch of State Highway 37 known as the Kula Highway. Running roughly 25 kilometres from the town of Pukalani to the Ulupalakua Vineyards, the Kula Highway isn’t particularly long, but it’s rife with worthy stops: botanical gardens, ranches, farmers’ markets and a surprising number of restaurants.

Kula Country Farms, photo by Alexandra Baackes

As I drive, I try (and fail) to keep my eyes on the road, enchanted by the mystical green swathes of the West Maui Mountains, their dark peaks shrouded in cloud.

I make a right on to Omaopio Road and arrive at Surfing Goat Dairy, where the namesake ruminants are known to take turns standing on a surfboard that sits in the middle of their pen. “They like the heights,” an employee tells me. After watching this display and feeding the goats some hay, I sit down to a tasty flight of goat cheese. More than just a farm, Surfing Goat Dairy makes and sells cheese and other items from its on-site shop (visitors can also book a tour of the facility or sign up to help with farm chores).

Driving back up to Highway 37, I continue on to Kula Country Farms, which I’m certain is the biggest roadside fruit stand I’ve ever seen. Produce-laden tables and tents spill out everywhere, all of them crowded with eager shoppers. I sample a Kula onion, fresh papaya and some strawberry pineapple jam, then cap my Upcountry trip just down the road with a stroll through the sprawling gardens, orchards and greenhouses of O’o Farms, which supply to a series of restaurants down the mountain in Lahaina.

Highway to Hana

Rainbow over Paia Bay, photo by Alexandra Baackes

Another day, I head for the far side of the island along Maui’s most storied route. The Hana Highway twists and turns for 100-plus kilometres. It begins in Kahului but really gets going after Paia, a hippie town that’s home to some of the best windsurfing conditions in the world, with huge waves rolling in off Paia Bay.

From Paia, the thin ribbon of road enters a thick canopy of tropical forest that covers the drive for most of the way. Seen from above, the Hana Highway looks like a cartoon snake, winding in and out with the undulations of the island; the route rounds some 620 curves and crosses 59 bridges (many of them one-laners) along the way.   

Along the road to Hana, photo by Alexandra Baackes

I steer the car under dense pockets of eucalyptus and bamboo, and nearly every corner I round yields a new sight: a quiet beach, a taro patch, a plunging waterfall. Around the halfway point, I stop for a hot dog and some shave ice at a simple roadside stand aptly named Halfway to Hana. As I turn right and continue along the highway, I grow slowly accustomed to its distinct rhythms and rules, including the etiquette for crossing those one-lane bridges: drive up to the white line and, if the coast looks clear, jam on the gas.

Eventually, I emerge on the far side of the island, passing the Pua’a Ka’a State Wayside—a popular swim spot on hot days—and arriving in Hana a few minutes later. Suddenly, it feels like I’ve driven not just all day, but back in time.

I wander the tiny town, which is strung along a single road. The local, somewhat ramshackle grocery store is selling T-shirts boasting that Hana is “far from Waikiki.”

I certainly agree: Hana feels like a place apart.

West Maui Beaches

Surfers gather at Grandma’s Beach, photo by Rachel Olsson

My final island road trip involves touring the paradise beaches of West Maui. Leaving Lahaina, I drive up the Honoapiilani Highway. With the mountains on my right, their peaks still shrouded in cloud, I pass the high-rise hotels of Kaanapali on my left, soon turning toward the sea and leaving the main highway.

Heading north, I roll along the coast, taking in the local vibe that permeates the slow and scenic Lower Honoapiilani Road, a barely-wide-enough thoroughfare that teems with trucks weighed low with surfboards. I could easily drive its full length in less than half an hour, but the allure of the many locally loved beach parks along the way makes for a much longer excursion.

Napili Bay and Beach, photo by David Fleetham/Alamy

Following the recommendation of several island residents. I stop at the legendary Pohaku Park, known locally as S-Turns (named for the formerly treacherous curve in the road that has since been straightened). The sounds of happy chatter and the aroma of grilled shrimp cooking on charcoal barbecues fill the air as I stroll along the tiny, crescent-shaped beach and peer out to the whitecaps, where local surfers are hanging ten.

Further up the road, I jam my car into a tiny parking place, which is really just a gap in a long line of vehicles crammed along the shoulder, and follow the crowds to Napili Bay. Soon I am sitting among the sun-worshipers, relaxing on a grand sweep of sand that’s girded by black volcanic outcrop. Stand-up paddleboarders are plying the calm turquoise waters beyond, and every now and then I spot a snorkel poking through the surface. It’s a quintessential Maui scene—and I’m happy to be taking it in.

Read more: Three Hawaiian Road Trips to Take

[This story appears in the October 2017 issue of WestJet Magazine]